Trifluoroacetic acid → benzyl 4-[(1H-indazol-5-ylamino)sulfonyl]piperidine-1-carboxylate

HRID 1269772Notes

Reaction equation

HRID 1269772 reaction equation
FC(F)(F)C(O)=O.O1CCCCC1[N:14]1[C:22]2[C:17](=[CH:18][C:19]([NH:23][S:24]([CH:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:34])[CH2:29][CH2:28]3)(=[O:26])=[O:25])=[CH:20][CH:21]=2)[CH:16]=[N:15]1>C(Cl)Cl>[NH:14]1[C:22]2[C:17](=[CH:18][C:19]([NH:23][S:24]([CH:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:34])[CH2:29][CH2:28]3)(=[O:26])=[O:25])=[CH:20][CH:21]=2)[CH:16]=[N:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69431167benzyl 4-{[(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)amino]sulfonyl}-1-piperidinecarboxylate

Product 1

HCID 18447213benzyl 4-[(1H-indazol-5-ylamino)sulfonyl]piperidine-1-carboxylateYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5.0 ml) was added to a solution of benzyl 4-{[(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)amino]sulfonyl}-1-piperidinecarboxylate (500 mg, 1.00 mmol) in methylene chloride (50 ml) at room temperature and stirred for 2 hours. After the reaction solution was concentrated, a saturated aqueous sodium hydrogencarbonate solution was added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=50/1) to obtain benzyl 4-[(1H-indazol-5-ylamino)sulfonyl]piperidine-1-carboxylate (317 mg, 76%).

Workup

  1. concentrationAfter the reaction solution was concentrated
  2. additiona saturated aqueous sodium hydrogencarbonate solution was added
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customresulting residue
  8. customwas purified by a silica gel column chromatography (eluent: chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-504c2dee442441f0862d322eeabd25b4
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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